Dimethylformamide → methyl (4E)-4-[[4-[[5-methyl-2-(thiophen-2-ylmethyl)-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 1070162Notes

Reaction equation

HRID 1070162 reaction equation
ClCC1N=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)OC=1C.[OH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:43][N:44](C)[CH:45]=[O:46].[C:48](OCC)(=O)[CH3:49].[CH3:54]CCCCC>O>[CH3:48][C:49]1[O:46][C:45]([CH2:5][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:44][C:43]=1[CH2:54][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 50764914-(Chloromethyl)-5-methyl-2-(thiophen-2-yl)-1,3-oxazoleHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 22344623methyl (4E)-4-[[4-[[5-methyl-2-(thiophen-2-ylmethyl)-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoateYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(chloromethyl)-5-methyl-2-(2-thienyl)oxazole (376 mg), methyl E-4-[(4-hydroxybenzyloxy)imino]-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 40 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[4-[5-methyl-2-(2-thenyl)-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyrate (495 mg, yield 63%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0d87650deb5442091c0f11af2099ee3
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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